Cheapest return flights from Chicago to San Juan in December from $456

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in December 2026 (see full year).

Return flights

02 Dec - 09 Dec Delta
18 Dec - 23 Dec Porter Airlines (Canada) Ltd
26 Dec - 03 Jan Porter Airlines (Canada) Ltd
19 Dec - 24 Dec WestJet
19 Dec - 27 Dec Porter Airlines (Canada) Ltd
22 Dec - 01 Jan WestJet

Also check the deals for one-way flights from Chicago to San Juan in December.

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The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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